Methyl p-toluenesulfonate → HCID 178433612, compound

HRID 2242536Notes

Reaction equation

HRID 2242536 reaction equation
[CH3:1][C:2]1[O:3][C:4]2[C:5]([N:14]=1)=[N:6][C:7]1[CH:8]=[CH:9][CH:10]=[CH:11][C:12]=1[CH:13]=2.[S:15]([C:20]1[CH:26]=[CH:25][C:23]([CH3:24])=[CH:22][CH:21]=1)([O:18][CH3:19])(=[O:17])=[O:16]>>[S:15]([C:20]1[CH:26]=[CH:25][C:23]([CH3:24])=[CH:22][CH:21]=1)([O-:18])(=[O:17])=[O:16].[CH3:1][CH:2]1[NH+:14]=[C:5]2[N:6]([CH3:19])[C:7]3[CH:8]=[CH:9][CH:10]=[CH:11][C:12]=3[CH:13]=[C:4]2[O:3]1

Participants

3

Reactant 2

HCID 6645Methyl p-toluenesulfonateHCID 222668482-Methyloxazolo[4,5-b]quinoline

Product 1

HCID 178433612HCID 178433612, compound

Procedure

A mixture of 0.6 g of 2-amino-3-hydroxyquinoline, 3.8 mL of trimethylorthoacetate and 0.1 g of p-toluenesulfonic acid is heated at 60° C. for 7 hours. The reaction mixture is then diluted with ethyl acetate, washed with sodium bicarbonate, and purified by column chromatography on silica gel to yield 0.28 g of 2-methyloxazolo[4,5-b]quinoline. The quinoline is heated with one equivalent of methyl tosylate at 70° C. for one hour to generate the product.

Sources & evidence

ORD record
ord-76aaf99a801e48a097341f37f4579ab6
Source dataset
uspto-grants-2010_03
Patent number
US07671214B2

Reaction notes

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